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| League History Index | Players | Teams | Managers | Leagues | Leaderboards | Awards | Accomplishments |
| Rank | Player | W | YEAR | Open Season Leaderboard |
|---|---|---|---|---|
| 1 | Eric Hacker | 49 | 2017-2022 | |
| 2 | William Cuevas# | 35 | 2016-2021 | |
| 3 | Logan Darnell | 32 | 2013-2024 | |
| 3 | Mark Leiter Jr.# | 32 | 2015-2021 | |
| 5 | Zack Trageton# | 31 | 2020-2025 | |
| 6 | Tyler Rogers# | 30 | 2015-2017 | |
| 7 | Eric Jokisch# | 28 | 2024-2025 | |
| 7 | Branden Kline | 28 | 2014-2016 | |
| 9 | Jordan Guerrero# | 26 | 2017-2025 | |
| 9 | Conor Harber | 26 | 2016-2021 | |
| 9 | Chad Kuhl# | 26 | 2023-2025 | |
| 12 | Domingo Acevedo# | 25 | 2016-2018 | |
| 12 | Pearson McMahan# | 25 | 2023-2025 | |
| 14 | Patrick Francescon | 24 | 2013-2015 | |
| 14 | Jacob Lee | 24 | 2014-2016 | |
| 16 | Simeon Woods Richardson# | 23 | 2020-2024 | |
| 17 | John Cornely | 22 | 2013-2017 | |
| 17 | Jimmy Gillheeney | 22 | 2013-2015 | |
| 17 | Jay Jackson# | 22 | 2013-2021 | |
| 17 | James Marvel | 22 | 2021-2023 | |
| 17 | Dillon Peters# | 22 | 2023-2024 | |
| 17 | Travis Radke | 22 | 2016-2019 | |
| 23 | Justin Ferrell | 21 | 2018-2019 | |
| 23 | Jake Jewell# | 21 | 2017-2025 | |
| 23 | Pierce Johnson# | 21 | 2014-2015 | |
| 23 | Ryan O'Rourke | 21 | 2014-2022 | |
| 23 | Tyler Phillips# | 21 | 2019-2020 | |
| 23 | Tyler Pill | 21 | 2014-2019 | |
| 23 | Logan Rinehart# | 21 | 2021-2024 | |
| 23 | Tayler Scott# | 21 | 2016-2019 | |
| 23 | Tanner Tully# | 21 | 2018-2021 | |
| 32 | Casey Bloomquist | 20 | 2018-2023 | |
| 32 | Luis Diaz | 20 | 2015-2017 | |
| 32 | Dylan Floro# | 20 | 2014-2016 | |
| 32 | Matt Purke | 20 | 2014-2017 | |
| 36 | Raudel Lazo | 19 | 2014-2017 | |
| 36 | Jake Lyons# | 19 | 2020-2025 | |
| 36 | Zachary Nuding | 19 | 2014-2016 | |
| 36 | Brady Puckett# | 19 | 2019-2025 | |
| 36 | Tommy Sommer# | 19 | 2023-2025 | |
| 36 | Cory Taylor | 19 | 2017-2020 | |
| 42 | Randy Bell# | 18 | 2019-2025 | |
| 42 | Ryan Carpenter# | 18 | 2013-2025 | |
| 42 | Frank Duncan | 18 | 2017-2021 | |
| 42 | Tyler Glasnow# | 18 | 2014-2015 | |
| 42 | David Hill | 18 | 2017-2019 | |
| 42 | Christopher Kirsch | 18 | 2016-2017 | |
| 42 | Marcelo Martinez# | 18 | 2020-2021 | |
| 42 | Luis Mateo | 18 | 2014-2017 | |
| 42 | Matthew Tracy | 18 | 2013-2014 | |
| 42 | Julio Urias# | 18 | 2015-2016 | |
| 52 | Sam Bachman# | 17 | 2022-2024 | |
| 52 | Beau Burrows# | 17 | 2018-2025 | |
| 52 | Brock Dykxhoorn | 17 | 2017-2023 | |
| 52 | Blayne Enlow# | 17 | 2020-2025 | |
| 52 | Chris Jensen | 17 | 2016-2018 | |
| 52 | Bud Jeter | 17 | 2015-2020 | |
| 52 | Gennison Reyes | 17 | 2015-2018 | |
| 52 | Austin Ross | 17 | 2013-2014 | |
| 52 | Jose Urena# | 17 | 2013-2019 | |
| 52 | Cole Winn# | 17 | 2023-2024 | |
| 62 | Brady Aiken | 16 | 2018-2019 | |
| 62 | Luke Albright# | 16 | 2023-2025 | |
| 62 | Matt Allan# | 16 | 2021-2023 | |
| 62 | D.J. Baxendale | 16 | 2016-2017 | |
| 62 | Jack Carey# | 16 | 2023-2025 | |
| 62 | Derek Casey# | 16 | 2022-2025 | |
| 62 | Odrisamer Despaigne# | 16 | 2023-2024 | |
| 62 | Deivi Garcia# | 16 | 2022-2025 | |
| 62 | Ryan Lillie | 16 | 2020-2021 | |
| 62 | Brett McKinney | 16 | 2016-2017 | |
| 62 | James Reeves | 16 | 2019-2023 | |
| 62 | Luis Reyes# | 16 | 2020-2025 | |
| 62 | Kraig Sitton | 16 | 2015-2017 | |
| 62 | Giovanni Soto | 16 | 2013-2014 | |
| 76 | Trevor Clifton# | 15 | 2018-2019 | |
| 76 | Alec Gamboa# | 15 | 2023-2025 | |
| 76 | Brett Graves | 15 | 2017-2021 | |
| 76 | Brett Kennedy# | 15 | 2018-2025 | |
| 76 | Rainy Lara | 15 | 2014-2017 | |
| 76 | Reid Love | 15 | 2018-2023 | |
| 76 | Kevin McGowan | 15 | 2018-2020 | |
| 76 | Trevor Megill# | 15 | 2019-2021 | |
| 76 | Dane Myers# | 15 | 2021-2023 | |
| 76 | Justin Nicolino | 15 | 2014-2014 | |
| 76 | Henry Owens | 15 | 2013-2014 | |
| 76 | Emilio Pagan# | 15 | 2016-2018 | |
| 76 | Yacksel Rios# | 15 | 2021-2023 | |
| 76 | Colin Rodgers | 15 | 2015-2017 | |
| 76 | Dalton Stambaugh# | 15 | 2022-2025 | |
| 76 | Joander Suarez# | 15 | 2024-2024 | |
| 76 | Corey Taylor | 15 | 2016-2017 | |
| 76 | Drew Verhagen# | 15 | 2020-2021 | |
| 76 | Cody Wheeler | 15 | 2013-2015 | |
| 95 | Brett Adcock# | 14 | 2018-2021 | |
| 95 | Blake Bass | 14 | 2016-2022 | |
| 95 | Jonathan Bowlan# | 14 | 2020-2021 | |
| 95 | Gerardo Carrillo# | 14 | 2022-2022 | |
| 95 | Tucker Davidson# | 14 | 2018-2019 | |
| 95 | Dean Deetz | 14 | 2018-2020 |
